Madonna Singles Ranked, 21-30

Every few days or weeks, I pick a music artist or band, compile a chronological playlist of all of their singles (based on Wikipedia, Discogs and a few other sources) and then try to arrange that playlist in such a way that I like each song more than the previous song. Rearranging the songs is a never ending process so once I’m at a point where I think I’m pretty close to how I feel, I share the results with you 10 or so songs at a time. I’ve come to define “singles” in a pretty broad way so that it includes any song that was used to promote an album (via video or single) or any song that charted in a significant way. Generally speaking, I don’t include remixes or live versions of songs that were previously released as singles.

30. Material Girl

From 1984’s Like a Virgin, Second Single

Madonna did not write “Material Girl” and she has expressed regret over recording it because the song title has become an oft-used nickname for her. The lyrics were intended to be ironic but I don’t know that anyone other than Madonna and the songwriters realized this. I certainly did not until I read excerpts of her interviews about the song. I’m not saying my irony meter is perfect, but I can usually spot it. Regardless of how the lyrics was perceived, the song was a huge hit and (after the ginormous success of “Like a Virgin”) cemented Madonna’s place as a pop superstar. Inadvertently, it provided something for Madonna to artistically react against on a number of future songs (“Express Yourself,” “Papa Don’t Preach” and “Love Spent” are among the many songs that explore the idea that money isn’t really all that important if you have love and are willing to work for it). I despised this song back in 1984 and still have an almost overwhelming negative visceral reaction to it when I hear the opening notes but when I make myself get past that, I really quite enjoy the song. Its a tight, well constructed Nile Rodgers’ produced number from his peak decade as a producer.

29. Impressive Instant

From 2000’s Music, Promotional Single

At some point in the early 2000’s, one of my students used a song from Music in an acting class project. She brought the CD in so we could play the song (because that’s what you did in those days) and never picked it up again. I stumbled across it again while cleaning my office about ten years ago and added it to my iTunes library. “Impressive Instant” came up several times on random shuffle and I eventually gave it five stars. This is a track that needs to be played loud every single time. Like just blast it. Warn your pets. Madonna’s three main super-powers are boundless charisma, the preternatural ability to recognize what is hot just as its becoming hot and a well honed instinct for selecting the right collaborators. Madonna made Music with producers William Orbit and Mirwais Ahmadzai. Ahmadzai had had a successful career in punk and dance for a couple decades in France before Madonna “discovered” him. This song is one of his main contributions to the album and it pretty much rocks. Part of the reason why Madonna’s career has been as long and successful as its been is that she recognizes good work when she hears it.

28. Frozen

From 1998’s Ray of Light, First Single

Ray of Light is pretty much my favorite Madonna album. If you need a Rosetta Stone for understanding how I feel about her music, this album would pretty much be it. This was not Madonna’s first foray into techo and electronica (nor her last) but at the time, it was her most consistently breathtaking record. Every track felt like a revelation to me. The record still sounds great but it now suffers from Influential Record Syndrome – enough people copied its success that it no longer sounds as bracingly original as it did back in the day. Other veteran artists (including, for example, U2) attempted to embrace electronica at the time but I don’t think anyone did it more successfully than Madonna. Hats off to her and producer/collaborator William Orbit. Additional Hat off to Madonna’s long-term co-writer Patrick Leonard.

“Frozen” opened the album. Its strikes an excellent balance between a lyric about a cold person and music that feels icy and distant. It was a bit of an odd choice for a lead single but, just as REM often released their oddest single first to make a statement, its as much a manifesto as it is a single. Madonna was letting the world know that her new album was by a new Madonna. Bold, brilliant and beautiful. Both her and the song.

27. Crazy for You

From the Soundtrack to the 1985 film Vision Quest, First Single

Its an oboe. “Crazy for You” is another song I sort of hated for years but hearing that little oboe for the first time made me listen to it differently. This was Madonna’s first major single foray into a different style of music – previously, everything she’d released had been dance pop. A ballad seemed like a bit of an unlikely stretch at the time (since many people thought she had a weak voice) but Madonna had another number one hit with the song. Lyrically, its a bit more sexual than I remember (I thought it was a pretty straightforward vanilla love song but if you pay attention to the lyrics, no, she’s singing about sex). More importantly, she really sells it – particularly the last chorus. She also uses her deeper register a couple of times on this song and sounds great.

If you’re not especially crazy about this song, I encourage you to sing along to the oboe parts uses the voice of Beeker from the Muppet show. Sharon discovered this the other day and it has enhanced my growing love for the song even more. Meep meep meep.

26. Miles Away

From 2008’s Hard Candy, Third Single

“Miles Away” has moved from around 92 to 26 over the time I’ve been working on this list. Its rapidly becoming one of my favorite Madonna songs of all time and its taken me a month of listening to it about every day to get there. Worth it. The lyric is really great – she jumps back and forth from talking about an actual physical gap between the lovers (he always loves her more when he’s miles away) and how that equates to an emotional gap between them when they are actually together. While the song was a little autobiographical (she and then husband Guy Ritchie were forced by their professional circumstances to have a long distance relationship from time to time), the situation described in the song is one that many of us are familiar with. I hear more than a touch of bitterness in Madonna’s voice as she sings this song which forms a compelling contrast with the driving dance beat that supports it. The chorus – especially the “miles away” repeats – makes me want to sing along (I do) and even dance (likewise). Really good stuff.

25. Bad Girl

From 1992’s Erotica, Third Single

When I read about how Madonna needed to “come back” after Erotica, I always get a little confused. Yes, this song peaked at 36 but it was the third single and the previous two singles from the album had both been top 10 (and the next one released in the USA – “Rain” – was top 20). I think writers are referring less to her chart success and more to how she was perceived by the media and general public. Society had reached “peak Madonna” around 1992 which meant our cultural tendency to reject people (especially women) who have had great success was starting to kick in. She didn’t need a “come back” due to fading commercial or artistic fortunes – she needed to change her image so that the public would forget she released a book called Sex featuring images of her with Vanilla Ice (among other people). Bah, humans. “Bad Girl” is one of the best songs on Erotica. Madonna celebrated sex with the title track but, on this one, she describes a character who is promiscuous (and a heavy drinker and smoker) as a way of wallpapering over pain and insecurity. The chorus is genuinely painful and the whole song is a great soul-searching ballad.

24. Music

From 2000’s Music, First Single

That video was the first time most Americans me Ali G and his creator Sacha Baron Cohen. “Music” is a kick-butt love letter to, well, music set to an irresistible beat. While one could rightly debate whether music does, indeed, make “the bourgeoisie free,” there’s no doubt that music truly does make the people come together. Madonna was apparently inspired to write this song after attending a Sting concert and watching the whole crowd come together when he started playing some of his work with the Police. Man, life is surreal.

23. Bitch I’m Madonna (featuring Nicki Minaj)

From 2015’s Rebel Heart, Third Single

I wasn’t crazy about Nicki Minaj was deployed on “Give Me All Your Luvin’,” but Madonna corrects that error here. Minaj is exactly the effect you need when you have a excellent in your face song and need the perfect thing to push the whole tune over the top. I generally love it when artists own their own bad self. Madonna’s first US Top 10 hit was in 1984. Her most recent US Top 10 Hit was in 2012. That’s 28 years of Top 10 hits. Dislike her music, dislike her image, but dude, respect is due to somebody with the ability to his the top 10 again and again and again over decades. She’s had number 1 dance tracks as recently as 2015. Anyhow, she has been criticized for a thousand different things in her career and instead of folding, she’s just moved on to create her next hit record. She’s Madonna.

So glad I get to write about this song. “Love Song” is a duet between Madonna and Prince that leans heavily on Prince’s style but Madonna sounds pretty great on the single. He was a co-producer on Like a Prayer and elements of his sound pops up on several tracks. While the song was obviously in extremely limited release as a single (acetate pressings can only survive about ten plays before they’re hopelessly degraded) it was played endlessly in 1990 on my headphones. Two great iconic musicians during one of their particularly fertile artistic periods? Yes please. One of many highlights from Like a Prayer, just a slightly higher highlight.

21. The Power of Good-Bye

From 1998’s Ray of Light, Fourth Single

Man, is is so hard to say no sometimes. Its even harder to walk away from something you’re invested in. So, see, I used to have this field of warts on my foot. I couldn’t get rid of them using any method. Went through a bad break-up and BAM all the warts were gone. Power of Goodbye. I’ve walked away from groups and projects that I’ve cared very much about because of what they were doing to my health and each time I’ve become healthier. Power of Goodbye. I’m not saying that I was following Madonna’s advice, but I do sing this song myself when I’m wondering about whether I really want to work on projects sometimes. Hey, in each of those cases I mention, the other person or group benefited from my absence, too. Power of Goodbye. Ending things hurts, saying no to great projects is always sad, but part of who you are as a person is determined by what you decide not to do. Great lyric, great song, personally meaningful to me.

Coming Soon: Two of my three favorite Madonna songs from film soundtracks.